RO120904B1 - Procedeu pentru prepararea oxo-alcoolilor superiori din amestecuri de olefine, prin hidroformilare în două etape - Google Patents

Procedeu pentru prepararea oxo-alcoolilor superiori din amestecuri de olefine, prin hidroformilare în două etape Download PDF

Info

Publication number: RO120904B1
Authority: RO; Romania
Prior art keywords: hydroformylation; process according; catalyst; distillation; hydrogenation
Prior art date: 1998-09-16

Application number

RO99-00987A

Other languages

English (en)

Romanian (ro)

Inventor

Alfred Kaizik

Bernhard Scholz

Walter Totsch

Wilfried Buschken

Franz Nierlich

Dirk Rottger

Klaus-Diether Wiese

Original Assignee

Oxeno Olefinchemie Gmbh

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1998-09-16

Filing date

1999-09-16

Publication date

2006-09-29

1999-09-16 Application filed by Oxeno Olefinchemie Gmbh filed Critical Oxeno Olefinchemie Gmbh

2006-09-29 Publication of RO120904B1 publication Critical patent/RO120904B1/ro

Links

238000007037 hydroformylation reaction Methods 0.000 title claims abstract description 93
239000000203 mixture Substances 0.000 title claims abstract description 90
150000001336 alkenes Chemical class 0.000 title claims abstract description 66
239000004435 Oxo alcohol Substances 0.000 title claims abstract description 5
JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical class OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 title claims abstract description 5
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title abstract description 10
238000004519 manufacturing process Methods 0.000 title abstract 2
239000003054 catalyst Substances 0.000 claims abstract description 84
238000005984 hydrogenation reaction Methods 0.000 claims abstract description 48
238000009835 boiling Methods 0.000 claims abstract description 33
238000004821 distillation Methods 0.000 claims abstract description 30
239000011541 reaction mixture Substances 0.000 claims abstract description 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 18
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
229930195734 saturated hydrocarbon Natural products 0.000 claims abstract description 8
229910052703 rhodium Inorganic materials 0.000 claims abstract description 5
239000010948 rhodium Substances 0.000 claims abstract description 5
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract description 5
238000000034 method Methods 0.000 claims description 40
229910017052 cobalt Inorganic materials 0.000 claims description 20
239000010941 cobalt Substances 0.000 claims description 20
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 17
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 15
239000010949 copper Substances 0.000 claims description 8
239000007791 liquid phase Substances 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 7
239000011651 chromium Substances 0.000 claims description 7
229910052802 copper Inorganic materials 0.000 claims description 7
229910052759 nickel Inorganic materials 0.000 claims description 7
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 6
229910052783 alkali metal Inorganic materials 0.000 claims description 6
150000001340 alkali metals Chemical class 0.000 claims description 6
229910052804 chromium Inorganic materials 0.000 claims description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
239000007788 liquid Substances 0.000 claims description 3
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 3
235000012239 silicon dioxide Nutrition 0.000 claims description 2
239000000377 silicon dioxide Substances 0.000 claims description 2
239000000306 component Substances 0.000 claims 4
150000001875 compounds Chemical class 0.000 claims 4
239000012876 carrier material Substances 0.000 claims 1
150000001298 alcohols Chemical class 0.000 abstract description 27
230000022244 formylation Effects 0.000 abstract 1
238000006170 formylation reaction Methods 0.000 abstract 1
239000007789 gas Substances 0.000 description 23
238000006243 chemical reaction Methods 0.000 description 21
150000001299 aldehydes Chemical class 0.000 description 18
239000000047 product Substances 0.000 description 18
230000015572 biosynthetic process Effects 0.000 description 17
238000003786 synthesis reaction Methods 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000000463 material Substances 0.000 description 9
229910052799 carbon Inorganic materials 0.000 description 6
230000009257 reactivity Effects 0.000 description 6
238000000926 separation method Methods 0.000 description 6
150000002148 esters Chemical class 0.000 description 5
238000004817 gas chromatography Methods 0.000 description 5
229910052751 metal Inorganic materials 0.000 description 5
239000002184 metal Substances 0.000 description 5
239000012071 phase Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
WEPNJTDVIIKRIK-UHFFFAOYSA-N 2-methylhept-2-ene Chemical class CCCCC=C(C)C WEPNJTDVIIKRIK-UHFFFAOYSA-N 0.000 description 4
QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
238000005755 formation reaction Methods 0.000 description 4
KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
229910002091 carbon monoxide Inorganic materials 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical class CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 3
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000012188 paraffin wax Substances 0.000 description 3
239000011148 porous material Substances 0.000 description 3
239000000243 solution Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
-1 41 olefins Chemical class 0.000 description 2
QDTDKYHPHANITQ-UHFFFAOYSA-N 7-methyloctan-1-ol Chemical class CC(C)CCCCCCO QDTDKYHPHANITQ-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
239000012018 catalyst precursor Substances 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
229940011182 cobalt acetate Drugs 0.000 description 2
QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 2
230000007423 decrease Effects 0.000 description 2
238000010586 diagram Methods 0.000 description 2
238000006471 dimerization reaction Methods 0.000 description 2
238000005485 electric heating Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
150000004675 formic acid derivatives Chemical class 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical class CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
239000002243 precursor Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000012266 salt solution Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000000758 substrate Substances 0.000 description 2
238000005829 trimerization reaction Methods 0.000 description 2
PYLMCYQHBRSDND-SOFGYWHQSA-N (E)-2-ethyl-2-hexenal Chemical compound CCC\C=C(/CC)C=O PYLMCYQHBRSDND-SOFGYWHQSA-N 0.000 description 1
GVRWIAHBVAYKIZ-FNORWQNLSA-N (e)-dec-3-ene Chemical compound CCCCCC\C=C\CC GVRWIAHBVAYKIZ-FNORWQNLSA-N 0.000 description 1
YITMLDIGEJSENC-HWKANZROSA-N (e)-hexadec-2-ene Chemical compound CCCCCCCCCCCCC\C=C\C YITMLDIGEJSENC-HWKANZROSA-N 0.000 description 1
IUPJSFOHUQGEDR-UHFFFAOYSA-N 1,3-dioxetanedione Chemical class O=C1OC(=O)O1 IUPJSFOHUQGEDR-UHFFFAOYSA-N 0.000 description 1
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
JHWIEAWILPSRMU-UHFFFAOYSA-N 2-methyl-3-pyrimidin-4-ylpropanoic acid Chemical compound OC(=O)C(C)CC1=CC=NC=N1 JHWIEAWILPSRMU-UHFFFAOYSA-N 0.000 description 1
MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 1
IRUDSQHLKGNCGF-UHFFFAOYSA-N 2-methylhex-1-ene Chemical compound CCCCC(C)=C IRUDSQHLKGNCGF-UHFFFAOYSA-N 0.000 description 1
FBEDQPGLIKZGIN-UHFFFAOYSA-N 2-methyloct-1-ene Chemical compound CCCCCCC(C)=C FBEDQPGLIKZGIN-UHFFFAOYSA-N 0.000 description 1
ZQDPJFUHLCOCRG-UHFFFAOYSA-N 3-hexene Chemical compound CCC=CCC ZQDPJFUHLCOCRG-UHFFFAOYSA-N 0.000 description 1
RITONZMLZWYPHW-UHFFFAOYSA-N 3-methylhex-1-ene Chemical compound CCCC(C)C=C RITONZMLZWYPHW-UHFFFAOYSA-N 0.000 description 1
XZJZVNABSFJYOK-UHFFFAOYSA-N 3-methylidenenonane Chemical compound CCCCCCC(=C)CC XZJZVNABSFJYOK-UHFFFAOYSA-N 0.000 description 1
GLUPFQMLFXGTNL-UHFFFAOYSA-N 3-methyloct-1-ene Chemical compound CCCCCC(C)C=C GLUPFQMLFXGTNL-UHFFFAOYSA-N 0.000 description 1
XWJMQJGSSGDJSY-UHFFFAOYSA-N 4-methyloct-1-ene Chemical compound CCCCC(C)CC=C XWJMQJGSSGDJSY-UHFFFAOYSA-N 0.000 description 1
YITMLDIGEJSENC-UHFFFAOYSA-N Hexadecen Natural products CCCCCCCCCCCCCC=CC YITMLDIGEJSENC-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000001273 butane Substances 0.000 description 1
IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
150000001844 chromium Chemical class 0.000 description 1
150000001869 cobalt compounds Chemical class 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
239000003599 detergent Substances 0.000 description 1
SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
229940069096 dodecene Drugs 0.000 description 1
238000005265 energy consumption Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
239000007792 gaseous phase Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
238000009434 installation Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000011068 loading method Methods 0.000 description 1
VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
150000005673 monoalkenes Chemical class 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
HWYHDWGGACRVEH-UHFFFAOYSA-N n-methyl-n-(4-pyrrolidin-1-ylbut-2-ynyl)acetamide Chemical compound CC(=O)N(C)CC#CCN1CCCC1 HWYHDWGGACRVEH-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
MOGJOLMSQWGXPA-UHFFFAOYSA-N nonyl formate Chemical class CCCCCCCCCOC=O MOGJOLMSQWGXPA-UHFFFAOYSA-N 0.000 description 1
238000006384 oligomerization reaction Methods 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000008188 pellet Substances 0.000 description 1
150000003003 phosphines Chemical class 0.000 description 1
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
239000001294 propane Substances 0.000 description 1
239000012495 reaction gas Substances 0.000 description 1
230000036632 reaction speed Effects 0.000 description 1
230000003134 recirculating effect Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
PXLIDIMHPNPGMH-UHFFFAOYSA-N sodium chromate Chemical compound [Na+].[Na+].[O-][Cr]([O-])(=O)=O PXLIDIMHPNPGMH-UHFFFAOYSA-N 0.000 description 1
238000005507 spraying Methods 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/02—Monohydroxylic acyclic alcohols
- C07C31/125—Monohydroxylic acyclic alcohols containing five to twenty-two carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
- C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxo-reaction combined with reduction
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

RO99-00987A 1998-09-16 1999-09-16 Procedeu pentru prepararea oxo-alcoolilor superiori din amestecuri de olefine, prin hidroformilare în două etape RO120904B1 (ro)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19842368A DE19842368A1 (de)	1998-09-16	1998-09-16	Verfahren zur Herstellung von höheren Oxoalkoholen aus Olefingemischen durch zweistufige Hydroformylierung

Publications (1)

Publication Number	Publication Date
RO120904B1 true RO120904B1 (ro)	2006-09-29

Family

ID=7881137

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
RO99-00987A RO120904B1 (ro)	1998-09-16	1999-09-16	Procedeu pentru prepararea oxo-alcoolilor superiori din amestecuri de olefine, prin hidroformilare în două etape

Country Status (18)

Country	Link
US (1)	US6331657B1 (de)
EP (1)	EP0987243B1 (de)
JP (1)	JP2000095717A (de)
KR (1)	KR100618929B1 (de)
CN (1)	CN1170800C (de)
AR (1)	AR020446A1 (de)
AT (1)	ATE228989T1 (de)
BR (1)	BR9904166A (de)
CA (1)	CA2282148A1 (de)
DE (2)	DE19842368A1 (de)
ES (1)	ES2185283T3 (de)
ID (1)	ID23134A (de)
MY (1)	MY126454A (de)
PL (1)	PL335432A1 (de)
RO (1)	RO120904B1 (de)
SG (1)	SG88756A1 (de)
TW (1)	TWI252225B (de)
ZA (1)	ZA995926B (de)

Families Citing this family (42)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE10034360A1 (de) *	2000-07-14	2002-01-24	Oxeno Olefinchemie Gmbh	Mehrstufiges Verfahren zur Herstellung von Oxo-Aldehyden und/oder Alkoholen
DE10058383A1 (de) *	2000-11-24	2002-05-29	Oxeno Olefinchemie Gmbh	Neue Phosphininverbindungen und deren Metallkomplexe
DE10062448A1 (de)	2000-12-14	2002-06-20	Oxeno Olefinchemie Gmbh	Verfahren zur Hydrierung von Hydroformylierungsgemischen
DE10135906A1 (de)	2001-07-24	2003-02-06	Oxeno Olefinchemie Gmbh	Verfahren zur Hydroformylierung von höheren Olefinen mit Kobaltverbindungen als Katalysator
US6774275B2 (en) *	2001-08-21	2004-08-10	Catalytic Distillation Technologies	Pulse flow reaction
AU2002327859B2 (en) *	2001-09-26	2007-08-09	Evonik Degussa Gmbh	Phthalic acid alkylester mixtures with controlled viscosity
DE10149348A1 (de)	2001-10-06	2003-04-10	Oxeno Olefinchemie Gmbh	Verfahren zur Herstellung von 1-Olefin mit Palladiumcarbenverbindungen
DE10210918B4 (de)	2002-03-13	2004-06-03	Oxeno Olefinchemie Gmbh	Verfahren zur Herstellung von Bisphosphiten
CN100503542C (zh)	2002-03-15	2009-06-24	奥克森诺奥勒芬化学股份有限公司	烯烃的加氢甲酰基化方法
DE10220801A1 (de) *	2002-05-10	2003-11-20	Oxeno Olefinchemie Gmbh	Verfahren zur Rhodium-katalysierten Hydroformylierung von Olefinen unter Reduzierung der Rhodiumverluste
DE10223593A1 (de) *	2002-05-27	2003-12-11	Degussa	Hydroxydiphosphine und deren Verwendung in der Katalyse
DE10225565A1 (de)	2002-06-10	2003-12-18	Oxeno Olefinchemie Gmbh	Katalysator und Verfahren zur Hydrierung von aromatischen Verbindungen
CN1290814C (zh)	2002-08-31	2006-12-20	奥克森诺奥勒芬化学股份有限公司	通过烯属不饱和化合物的加氢甲酰基化制备醛的方法，该方法在环状碳酸酯存在的条件下由未改性的金属配合物催化
DE10327434A1 (de) *	2002-08-31	2004-03-04	Oxeno Olefinchemie Gmbh	Verfahren zur Hydroformylierung von olefinisch ungesättigten Verbindungen, insbesondere Olefinen in Gegenwart cyclischer Kohlensäureester
RU2337090C2 (ru)	2002-08-31	2008-10-27	Оксено Олефинхеми Гмбх	Способ гидроформилирования олефиновых соединений в присутствии циклических эфиров угольной кислоты
DE10257499A1 (de)	2002-12-10	2004-07-01	Oxeno Olefinchemie Gmbh	Verfahren zur Herstellung von 1-Olefinen durch katalytische Spaltung von 1-Alkoxyalkanen
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1998
- 1998-09-16 DE DE19842368A patent/DE19842368A1/de not_active Withdrawn
1999
- 1999-05-25 ID IDP990489A patent/ID23134A/id unknown
- 1999-06-22 TW TW088110454A patent/TWI252225B/zh not_active IP Right Cessation
- 1999-07-31 ES ES99115272T patent/ES2185283T3/es not_active Expired - Lifetime
- 1999-07-31 EP EP99115272A patent/EP0987243B1/de not_active Expired - Lifetime
- 1999-07-31 AT AT99115272T patent/ATE228989T1/de not_active IP Right Cessation
- 1999-07-31 DE DE59903635T patent/DE59903635D1/de not_active Expired - Fee Related
- 1999-09-10 SG SG9904462A patent/SG88756A1/en unknown
- 1999-09-13 JP JP11258860A patent/JP2000095717A/ja active Pending
- 1999-09-14 KR KR1019990039213A patent/KR100618929B1/ko not_active Expired - Fee Related
- 1999-09-14 CA CA002282148A patent/CA2282148A1/en not_active Abandoned
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- 1999-09-15 PL PL99335432A patent/PL335432A1/xx unknown
- 1999-09-15 US US09/396,371 patent/US6331657B1/en not_active Expired - Fee Related
- 1999-09-15 CN CNB991188632A patent/CN1170800C/zh not_active Expired - Fee Related
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Also Published As

Publication number	Publication date
PL335432A1 (en)	2000-03-27
EP0987243B1 (de)	2002-12-04
ATE228989T1 (de)	2002-12-15
CN1255479A (zh)	2000-06-07
US6331657B1 (en)	2001-12-18
MY126454A (en)	2006-10-31
CA2282148A1 (en)	2000-03-16
KR100618929B1 (ko)	2006-09-01
AR020446A1 (es)	2002-05-15
EP0987243A1 (de)	2000-03-22
JP2000095717A (ja)	2000-04-04
ID23134A (id)	2000-03-15
ES2185283T3 (es)	2003-04-16
KR20000023121A (ko)	2000-04-25
SG88756A1 (en)	2002-05-21
DE59903635D1 (de)	2003-01-16
TWI252225B (en)	2006-04-01
CN1170800C (zh)	2004-10-13
ZA995926B (en)	2000-04-04
DE19842368A1 (de)	2000-03-23
BR9904166A (pt)	2000-09-19

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